New York State Route 299 (NY 299) is a short but important state route entirely within Ulster County, New York, in the United States. Centered on its interchange with the New York State Thruway outside New Paltz, it provides access from that road to the popular recreational attractions of the Shawangunk Ridge to the west and Poughkeepsie to the east. Only the eastern section is a state highway; from Shawangunk to New Paltz, it is owned and maintained by Ulster County.

U.S. Route 44 (US 44) is an east–west United States Numbered Highway that runs for 237 miles (381 km) through four states in the Northeastern United States. The western terminus is at US 209 and New York State Route 55 (NY 55) in Kerhonkson, New York, a hamlet in the Hudson Valley region. The eastern terminus is at Route 3A in Plymouth, Massachusetts.